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An Efficient Synthetic Method to Nonnatural α ‐ and β ‐Tryptophan Analogues via Friedel‐Crafts Alkylation of Indoles with Nitroacrylates
Author(s) -
Sui Yong,
Liu Li,
Wang Dong,
Chen YongJun
Publication year - 2007
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.200790190
Subject(s) - chemistry , friedel–crafts reaction , alkylation , tryptophan , catalysis , organic chemistry , nitro , lewis acids and bases , combinatorial chemistry , amino acid , biochemistry , alkyl
The Friedel‐Crafts alkylation of indoles with nitroacrylates could provide α ‐ and β ‐tryptophan nitro‐precursors, respectively, in moderate to good yields under Lewis acid catalysis. The diastereoselectivities of the reaction were enhanced by using 2‐substituted indoles. The alkylation products could be easily transformed to nonnatural tryptophan derivatives.